Methanesulfonyl chloride → HCID 86672755, compound

HRID 1423065Notes

Reaction equation

HRID 1423065 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][S:20]([CH3:19])(=[O:22])=[O:21])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 86672755HCID 86672755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of (2-bromopyridin-4-yl)-methanol (3.00 g, 16.0 mmol) and DIPEA (8.3 mL, 48 mmol) in dichloromethane (30 mL) is added methanesulfonyl chloride (1.30 mL, 16.8 mmol). The resulting mixture is warmed to room temperature. After 1 hour, the mixture is diluted with dichloromethane (20 mL) and washed with saturated aqueous ammonium chloride (3×10 mL), saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated to afford crude methanesulfonic acid 2-bromopyridin-4-ylmethyl ester, which is used without purification.

Workup

  1. washwashed with saturated aqueous ammonium chloride (3×10 mL), saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a69dc61edfa6485bbaf7074045cc9895
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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